Synthesis of N-Squaramidoacids and Their Application in Asymmetric Borane Reduction of Prochiral Ketones  

作　　者：张骥 李蕾蕾 邹海华 陈君君 郁开北 谢如刚 

机构地区：[1]Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China [2]Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610061, China

出　　处：《Chinese Journal of Chemistry》2004年第6期585-589,共5页中国化学（英文版）

基　　金：Project supported by the National Natural Science Foundation of China (No. 20172038) and Youth Science Foundation of Sichuan University.

摘　　要：A series of novel N-squaramidoacid ligands were prepared conveniently. Without converting to corresponding amino alcohols, these ligands could be used in asymmetric borane reduction of prochiral aromatic ketones to give secondary alcohols in good to excellent enantiomeric excesses. The results showed that N-squaramidoacids are more efficient ligands than N-sulfonyl amino acids. N-Squaryl proline was proved to be an excellent ligand in this catalytic asymmetric process.A series of novel N-squaramidoacid ligands were prepared conveniently. Without converting to corresponding amino alcohols, these ligands could be used in asymmetric borane reduction of prochiral aromatic ketones to give secondary alcohols in good to excellent enantiomeric excesses. The results showed that N-squaramidoacids are more efficient ligands than N-sulfonyl amino acids. N-Squaryl proline was proved to be an excellent ligand in this catalytic asymmetric process.

关 键 词：amino acid squaramidoacid BORANE KETONE asymmetric reduction 

分 类 号：O621[理学—有机化学]